Chicago: Insider Travel Guide

Nora O'Donnell, for CNN • Updated 25th March 2017

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Editor's Note — CNN Insider Guides are thoroughly checked for accuracy. Given the fluid nature of the travel industry, however, some listings may fall out of date before guides can be updated. The best practice is to confirm current information on official websites before making plans to visit any business or attraction.

(CNN) — Ask anyone on the street what he or she likes most about Chicago, and you'll mostly likely get "the friendly people." But what makes Chicagoans so gosh darn friendly?

Perhaps it's the camaraderie they form during the city's harsh winters and blessed summers. Or maybe it's because this Midwestern giant has some of the best museums, restaurants and architecture in the world -- and it's all actually affordable.

Whatever the reason, there's nothing "second" about the Second City in the hearts of its citizens -- as well as most anyone else who's explored this paradoxically folksy metropolis.

Hotels

Luxury

Waldorf Astoria

Travel + Leisure frequently ranks the Waldorf Astoria (formerly the Elysian) as one of the top large-city hotels in the United States, and it's easy to see why: the lobby's glistening marble and starburst chandeliers rival the grandest beaux-arts hotels in Paris.

The 34-seat Bernard's Bar on the second floor serves an excellent $14 champagne cocktail, and the classic Coco Chanel vibe is worth the price tag.

If you forgot to pack your Chanel or Savile Row suits for the occasion, you can pick up appropriate attire at one of the spendy shops on Oak Street, just around the corner.

The Peninsula

Another top-ranked U.S. hotel, the Peninsula offers the amenities that one expects from a five-star spot, including an indoor pool worthy of an F. Scott Fitzgerald novel, afternoon tea service that surpasses the high tea at London's Savoy Hotel and a prime location in the center of the Magnificent Mile shopping district.

The spa services here are worth the price.

In 2012, Chicago magazine ranked it one of the top day spas in the city, where the massages (around $165 per hour) blew away the competition.

Mid-range

The Public

Unlike New York and Los Angeles, luxury hotels in downtown Chicago are generally cheaper (if not cheap), which means that mid-range rooms are even more of a bargain.

Built in 1926, the Ambassador East Hotel and its legendary Pump Room entertained the likes of Frank Sinatra and Judy Garland until it faded from the limelight.

Then in 2010, hotel developer (and Studio 54 cofounder) Ian Schrager bought the building and poured $35 million into its renovation.

Renamed the Public, the Gold Coast hotel has quickly reclaimed its throne as the home away from home for the rich and beautiful -- many of whom like to cluster around the white couches of the Library bar before heading to the revamped Pump Room.

Burnham Hotel

Recognize the name Burnham? That's Daniel Burnham, the legendary architect, city planner and protagonist in Erik Larson's bestseller Devil in the White City. Burnham's firm also had a hand in designing the historic Reliance Building, which houses the Hotel Burnham in the Loop.

Completed in 1895, the Reliance Building is noteworthy for its floor-to-ceiling plate glass windows, a groundbreaking concept at the time.

The interiors are a time warp, too, with elaborate metal elevator grilles, restored mosaic tile floors and tasteful touches of art nouveau splendor.

Budget

Inn at Longman & Eagle

In recent years, the Logan Square neighborhood in Northwest Chicago has exploded as a hot bed for affluent hipsters -- Longman & Eagle is the epicenter.

The inn has only six rooms, all outfitted with classy-but-kitchy design elements ripped from the pages of Wallpaper magazine (or perhaps inspired by the Portland chic of the Ace Hotel chain).

The best part of staying at the inn is a guaranteed spot at the restaurant downstairs.

The Michelin-rated gastropub doesn't take reservations otherwise, and the wait can be up to two hours at peak times.

Thompson's rising popularity (Johnny Depp is a fan, too) allowed him to open a second store in the historic Monadnock Building in the loop in 2012.

Optimo Hats, 10215 S. Western Ave.; +1 773 238 2999

Merz Apothecary

Since 1875, this family-run drugstore has been a haven for herbal remedies and European goods.

The original location in Lincoln Square still fills prescriptions and still uses its original antique pharmacy jars.

Need a bar of soap for your stay?

Merz has one of the largest collections of luxury bath products from around the world.

Attractions

The Modern Wing at the Art Institute of Chicago

Scott Olson/Getty Images North America/Getty Images

Like the Metropolitan Museum of Art in New York, you can spend an entire day at the Art Institute and cover only a fraction of the collection.

If time is limited, you can do a quick Ferris Bueller moment in the main building, before heading to the 264,000-square-foot Modern Wing to admire works by Matisse, Picasso and Miró under the natural light.

For lunch there's Tony Mantuano's elegant Terzo Piano on the third floor, where the spectacular view makes an advance reservation a necessity.

Chicago Architecture Foundation River Cruise

There are a number of boat tours on the Chicago River, but the Chicago Architecture Foundation River Cruise is the one that's most worth your time.

Enthusiastic CAF docents provide an engaging review of the city's rich architectural history, and the perspective from the water is unlike (and far superior to) anything you'd experience at street level.

Millennium Park

Shhh ... the park still thinks the millennium began in 2004.

Peter J. Schulz

Although it opened four years behind schedule in 2004 and many taxpayers grumbled at its half-billion-dollar price tag, Millennium Park has become a critical darling.

Photos in front of the mirrored Cloud Gate sculpture, or "The Bean" as most people call it, have become a staple for tourists and locals, and on hot summer days, the Crown Fountain is a refuge for barefoot children in bathing suits.

The Jay Pritzer Pavillion, designed by Frank Gehry, hosts a slew of outdoor performances all summer long, and the competition for free lawn space is fierce.

Comedy

Chicago's as notorious for wit as it is for wind.

You might catch tomorrow's biggest -- in many cases, literally -- comedians at one of Chi-Town's world-famous comedy labs.

The Second City

Name almost any SNL breakout star -- John Belushi, Chris Farley, Tina Fey, Amy Poehler -- and chances are he or she served a stint in Chicago at Second City.

Chicago is the best place in the world to experience improv and sketch comedy, and the Second City revue (nightly except Mondays) and Monday night's Improv All-Stars are safe bets that are always entertaining.

Those brave enough to test their improvisational skills are welcome to attend a drop-in class ($15; no experience required) at the training center on Sundays at 6 p.m.

iO

The iO is the true improv giant in town, and the theater's signature show, "The Harold," is the definitive improv experience.

Founders Del Close and Charna Halpern invented the Harold technique, in which performers take a suggestion from the audience and create scenes and characters on the spot.

The Neo-Futurists

The Neo-Futurists isn't improv or sketch; it's experimental theater mixed with moments of truth and hilarity.

Every weekend since 1988 the troupe has performed "Too Much Light Makes the Baby Go Blind," 30 short plays that are carried out in just 60 minutes.

Each play is written by the ensemble and the lineup is constantly changing.

No two performances are the same.

The absurdity of the format -- with performers dashing around the stage at breakneck speed -- is worth a million laughs.